Meeting women at bars, concerts, parties, and bookstores is far from unheard of. But of course there are some places and situations where trying to pick up a woman might not be the best idea. We’re here to assure you it can be done. Here are six popular situations and locales where you can swoon a potential lady friend, if you go about it the right way.

6 While she’s at work (and you’re not)Why it’s wrong: You may think it’s endearing to sort of stalk the smokin’ hot barista around the corner from your place or to “visit” your favorite cocktail waitress on a weekly basis and ask her a ton of personal questions while she cleans up drunk people’s messes. This is the opposite of a prime situation for Woman in Question to be in, though. The line between being sweet and aggressive is very, very thin, due to the fact that she can’t leave and she probably has to be nice to you because hey, that’s customer service — even though she might think you’re annoying and really want you to go away.

Do it right: Begin by altering your mindset. Rather than, “I’m going to Café X since amazing sexy woman works there,” think, “I’m going to Café X because I’m hungry for a sandwich… and it would be nice to also see amazing sexy woman, too.” Even if you’re really thinking the former, telling yourself this will give you a less-desperate and not-as-inexplicably-obsessed-with-sandwiches air. Go ahead, flirt her up, but be respectful of her space and time.

Once you’ve gotten to buddy-buddy level and have spent way too much money on lattes, then you can ask her if she’d be interested in hanging out some other time. Don’t ask her to hang out after her shift, ever. It’s annoying, and she might be afraid to walk to her car after bar close. Realize if she says no you might need to find a new place to buy sandwiches/coffee/records, so gauge the deliciousness, convenience, and place in general before asking her out.

5 The gymWhy it’s wrong: My spandex pants are giving me a slight case of camel toe, my glutes exercise is done in a similar position I’d take while taking it from behind, and I’m trying to watch the “Real Housewives” while simultaneously getting my cardiovascular fitness on. Women really, really appreciate sweaty, testosterone-amped men leaving them alone in the midst of working out.

Do it right: The territory of the gym where you’ll have a better chance of picking up a (fit) cutie is in yoga and/or Pilates classes. The atmosphere is more intimate (as opposed to predatory) and you’ll be subjecting yourself to the same awkward positions we are. There’s a ton of deep breathing involved, so everyone will be relaxed. Striking up conversations with neighboring mats before and after class is also super-natural — unlike Dude who I recently encountered awkwardly running backwards in order to chat with Hot Girl on the treadmill next to him (she was not impressed).

4 In a car or mode of public transportationWhy it’s wrong: Driving while distracted by pretty ladies is dangerous, one. Two, getting honked at/leered at on the subway is high on the list of pet peeves held by nearly every woman who graces this planet.

Do it right: You don’t need to avoid looking at her and then hope she responds to your Missed Connections post later. (Odds are, only 56 year-old men with goatees will answer those requests.) Instead, make eye contact and flash that award-winning smile. If she reciprocates with a kind-looking smirk, you’re in to make some witty remark about the book she’s reading, the duct tape on her car, etc. As always, you need to tune in to her body language: If she’s smiling, facing towards you, and answering your Qs with more than two-syllable words, continue honing that charm. On the other hand, if she looks bored as shit and won’t turn down her music, let it go and move on to the next car.

3 In a public bathroomWhy it’s wrong: Because it smells like urine, and if you’re at a bar (which you probably are), there’s that lingering stench of vomit, too. Oh, you also have a wee bit of TP stuck to the bottom of your shoe.

Do it right: First, do the shoe check. All clear? Great. Now, meet her gaze and come up with a brilliant greeting that ensures she’ll talk to you outside of the bathroom. Avoid backing her into any corners or asking open-ended questions. Simply say, “Hi,” while donning that gorgeous grin of yours. Then exit. Seriously, that’s all it takes. She’ll remember the cute nice dude who said hi when she was washing her hands because it’s unexpected and, ironically, refreshing, and she will most likely try to start a convo with you away from the piss-splattered toilets.

2 FacebookWhy it’s wrong: Holy hell, I’m not sure what’s creepier than getting random friend requests from mysterious men who I have absolutely no friends in common with at all and kind of live near my vicinity. But alas, I’m completely guilty of this Facebook faux pas, too. (I’ve recently started crushing on the guy who won the Big Buck Hunter Championship and sent him a friend request—along with 1,235 other people.) But will I ever see him in real, non-Facebook life? No, probably not (unfortunately).

Do it right: From the women I know who this has actually worked on (hallelujah for the socially-awkward, they do exist!), the relationship started with platonic messaging back and forth about common interests before a friend request was ever sent. Ex: “I’m new to the area and seeing who likes the same music as me.” Then they proceed to message back and forth about music before heading to a show together.

If you’re going to take the leap and friend request someone you “stumbled upon” who you have no friends in common with, you should include a quick two-sentence message in your request that includes 1) How you found her and 2) Something sweet that clearly communicates you’re not a psychopath who’s going to rifle through her photos for new masturbation material. So no “you’re hot” or “I liked your profile picture.” This still isn’t a hundred-percent assurance she’ll accept and not think you’re creepy. But hey, it’ll increase the likelihood of said acceptance. From there, it’s up to you to strike up a conversation that will probably be drawn out because it’s impossible to not scare someone by commenting on all of their pictures and statuses.

And, if you just want a resource to do all the work for you, there’s the new online dating site, Clique.com (right now it’s only for those living in NYC, but we’re thinking it should expand in the near-ish future) that matches you up with potential S.O.’s through your Facebook network.

1 On a date with someone elseWhy it’s wrong: Because to not pay 100 percent attention to the woman you’re actually supposed to be on a date with is just douche-y. But you should know that already… right?

Do it right: Yes, this sticky situation takes some tact. It isn’t impossible, though. We can cite at least one example of a happily, married-for-six-years couple who met while they were on a blind date — but not with each other. And they managed to not make their dates sob or feel horribly rejected in the process.

If you meet a special-seeming person while out with someone else, your major objective should be to first get through the date you’re on without being an asshole. See: Don’t chat the other girl up for more than a minute or try to buy her a drink. You need to just give her your info, or get hers, explain your situation (it’s okay to be vague!) and tell her you hope you’ll talk later. On the surface, this might seem like a player-esque, move. We’ve all been on dates that were less than enticing, though. If she’s empathetic, and you were subtle, you’ll be fine. Just don’t ask that initial girl on a date again, dick.

About Caitlin Thornton...
Caitlin Thornton is a writer living in Brooklyn. When she's not attached to her laptop or drinking coffee like an alcoholic, you can find the Chicago-native out urban exploring, buried in books authored by drugged-up writers she probably shouldn't admire, and avoiding eye contact with people on the subway. Thornton also writes for the hip DIY magazine, ReadyMade.

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Join The Discussion

In a public bathroom – WTF? Women enjoy having random creeps show up in the ladies' room to wash their hands and smile at them as they're coming out of the stall?

06.08.11 at 11:24 am

Color me surprised

Yeah, I agree – in a public bathroom? In a bar? I've got to meet Caitlin, she's a dirty girl!

06.08.11 at 2:42 pm

TaraB

Want to know the best place is "where you work". Because if she is around you alot she will get to know you better have something to talk to you about and you can have some awesome hide out places sex. Only problem if you screw it up yo will have to find a new job. lol

06.08.11 at 11:01 pm

John Doe

honestly…get rid of this cunt. She sucks at lists.

06.14.11 at 8:06 am

co2insanity

You forgot Anthony Weiner's Blackberry….

06.22.11 at 11:17 pm

jason gidago

yah gotta meet this girl. i like a freak in the public bathroom. hit me up CT

09.09.11 at 5:04 pm

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